Acetamide, N-5-1,2-bis(acetyloxy)ethyl-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 3S-3.alpha.,4.beta.,5.beta.(R*)-

Base Information

• Chemical Name: Acetamide, N-5-1,2-bis(acetyloxy)ethyl-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 3S-3.alpha.,4.beta.,5.beta.(R*)-
• CAS No.: 163916-56-1
• Molecular Formula: C₂₆H₃₂N₂O₆
• Molecular Weight: 468.55
• Mol file: 163916-56-1.mol

Synonyms:Acetamide, N-5-1,2-bis(acetyloxy)ethyl-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 3S-3.alpha.,4.beta.,5.beta.(R*)-

Chemical Property of Acetamide, N-5-1,2-bis(acetyloxy)ethyl-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 3S-3.alpha.,4.beta.,5.beta.(R*)-

Chemical Property:

• PSA: 94.17000
• LogP: 2.78450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Acetamide, N-5-1,2-bis(acetyloxy)ethyl-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 3S-3.alpha.,4.beta.,5.beta.(R*)-

There total 19 articles about Acetamide, N-5-1,2-bis(acetyloxy)ethyl-4-(phenylmethoxy)-1-(phenylmethyl)-3-pyrrolidinyl-, 3S-3.alpha.,4.beta.,5.beta.(R*)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

benzyl bromide (100-39-0) → 2-acetamido-5,6-di-O-acetyl-3-O-benzyl-1,4-(N-benzylimino)-1,2,4-trideoxy-D-glucitol (163916-56-1)

Guidance literature:

Multi-step reaction with 18 steps

1: 80percent oily NaH / dimethylformamide / Ambient temperature

2: 10percent aq. HOAc / methanol / 7 h / Ambient temperature

3: NaBH₄ / methanol / 1 h / Ambient temperature

4: pyridine / Ambient temperature

5: 1M aq. NaOH / methanol / 7 h / Heating

6: KHCO₃ / dioxane; H₂O / Ambient temperature

7: 85 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

8: 97 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

9: 94 percent / triethylamine / dimethylformamide / 40 h / 120 °C

10: 1M aq. NaOH / dioxane / 15 h / Heating

11: KHCO₃ / dioxane; H₂O / Ambient temperature

12: 100 percent / pyridine / 4 h / Ambient temperature

13: 67 percent / p-toluenesulfonic acid, dimethoxypropane / acetone / 6 h / Ambient temperature

14: 91 percent / NaOMe / methanol / 3.5 h / Ambient temperature

15: 83 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

16: 13 percent / benzylamine / 17 h / 50 °C

17: 10percent aq. HCl / methanol / Ambient temperature

18: pyridine / Ambient temperature

With hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; dimethoxypropane; sodium methylate; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; benzylamine; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)89338-8

Reference yield:

2-methyl-(3-O-benzyl-1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2.1-d>-2-oxazoline (125158-55-6) → 2-acetamido-5,6-di-O-acetyl-3-O-benzyl-1,4-(N-benzylimino)-1,2,4-trideoxy-D-glucitol (163916-56-1)

Guidance literature:

Multi-step reaction with 17 steps

1: 10percent aq. HOAc / methanol / 7 h / Ambient temperature

2: NaBH₄ / methanol / 1 h / Ambient temperature

3: pyridine / Ambient temperature

4: 1M aq. NaOH / methanol / 7 h / Heating

5: KHCO₃ / dioxane; H₂O / Ambient temperature

6: 85 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

7: 97 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

8: 94 percent / triethylamine / dimethylformamide / 40 h / 120 °C

9: 1M aq. NaOH / dioxane / 15 h / Heating

10: KHCO₃ / dioxane; H₂O / Ambient temperature

11: 100 percent / pyridine / 4 h / Ambient temperature

12: 67 percent / p-toluenesulfonic acid, dimethoxypropane / acetone / 6 h / Ambient temperature

13: 91 percent / NaOMe / methanol / 3.5 h / Ambient temperature

14: 83 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

15: 13 percent / benzylamine / 17 h / 50 °C

16: 10percent aq. HCl / methanol / Ambient temperature

17: pyridine / Ambient temperature

With hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; dimethoxypropane; sodium methylate; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; benzylamine; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)89338-8

Reference yield:

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline (117177-19-2) → 2-acetamido-5,6-di-O-acetyl-3-O-benzyl-1,4-(N-benzylimino)-1,2,4-trideoxy-D-glucitol (163916-56-1)

Guidance literature:

Multi-step reaction with 18 steps

1: 80percent oily NaH / dimethylformamide / Ambient temperature

2: 10percent aq. HOAc / methanol / 7 h / Ambient temperature

3: NaBH₄ / methanol / 1 h / Ambient temperature

4: pyridine / Ambient temperature

5: 1M aq. NaOH / methanol / 7 h / Heating

6: KHCO₃ / dioxane; H₂O / Ambient temperature

7: 85 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

8: 97 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

9: 94 percent / triethylamine / dimethylformamide / 40 h / 120 °C

10: 1M aq. NaOH / dioxane / 15 h / Heating

11: KHCO₃ / dioxane; H₂O / Ambient temperature

12: 100 percent / pyridine / 4 h / Ambient temperature

13: 67 percent / p-toluenesulfonic acid, dimethoxypropane / acetone / 6 h / Ambient temperature

14: 91 percent / NaOMe / methanol / 3.5 h / Ambient temperature

15: 83 percent / 4-dimethylaminopyridine / pyridine / Ambient temperature

16: 13 percent / benzylamine / 17 h / 50 °C

17: 10percent aq. HCl / methanol / Ambient temperature

18: pyridine / Ambient temperature

With hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; dimethoxypropane; sodium methylate; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; benzylamine; In 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)89338-8

upstream raw materials:

acetic anhydride

benzyl bromide

2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline

2-methyl-(3-O-benzyl-1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2.1-d>-2-oxazoline

Refernces